Holiday rentals with a pool in Windsor

The exterior of a modern cottage is displayed, featuring a patio area with seating for four under a shaded umbrella, a lounge area with cushioned seating, and easy access to the surrounding greenery. Large windows reflect the natural light, while a serene pond is visible in the background.

4.96 out of 5 average rating, 70 reviews

Cottage @ Rochester Place Golf Club and Resort

Modern cottage located on a pond with view of the 17th green in Rochester Place Golf Club and Resort. Guests have called our location serene as it is one of the most private cottages in the resort. Open concept with 2 bedrooms; sleeps 6 including a sofa bed. Dock your boat on the resort's canal where you then have access to beautiful Lake St. Clair. Golf on the 18 hole championship course. Enjoy a BBQ on our beautiful patio or take advantage of the many family amenities the resort has to offer.

4.89 out of 5 average rating, 87 reviews

The Cedarwood Suite features a modern design with a spacious bed adorned with a patterned coverlet. A flat-screen television is mounted on the wall opposite. Natural light filters through curtains, illuminating a small dining area equipped with a table and chairs.

Guest suite in Windsor

Cozy Cedarwood Suite ☆Terrace ☆ heated salt pool

Modern private suite with its own entrance and a gorgeous terrace. The space has a fully equipped kitchenette, a bathroom with shower. a 65" Roku HDTV : chromecast, Disney+, Netflix, Amazon Prime, ... The heated outdoor pool and a dining area with BBQ is accessible. These are shared with our family and guests. 20 minutes from the Detroit, Michigan border and downtown Windsor with its Caesars Casino. Ideal for a travelling couple or a contract worker looking for a cozy place to call home.

4.8 out of 5 average rating, 207 reviews

An inviting outdoor area showcases a glistening in-ground oval pool framed by a spacious deck. Comfortable lounge chairs are situated nearby, and the house features large windows that allow for ample natural light. A dining set is visible under the covered patio, ideal for outdoor meals.

Home in Riverside

Beautiful Oasis w/Heated Private Pool & Sunroom!

*HEATED POOL IS OPEN APRIL 1 - OCT 31* Welcome to Windsor’s largest and coziest stay! This gorgeous home blends modern design with comfort, featuring an inviting sunroom with soaring ceilings and natural light, perfect for morning coffee or quiet evenings. The chic decor creates a stylish, yet homey feel :) Unwind in a private backyard oasis with a 15x30, 8’ deep, in-ground oval pool with a brand NEW heater and BBQ lounge! Our backyard designed for a unique and relaxing family experience!

A spacious living area features a light-colored sectional sofa adorned with dark blue and white blankets. A rustic barn door, made of wood, adds character and leads to the bedroom. Two round mirrors are mounted on the wall, reflecting natural light.

4.94 out of 5 average rating, 154 reviews

Waterfront Luxurious Cottage in Lakeshore, Ontario

Waterfront Modern Executive Cottage with lots of natural light and stunning views. This cottage is a breath of fresh air and provides all of the comforts and conveniences that you need in a luxurious relaxing getaway . The cottage boasts a unique layout that sleeps 4 with a bright fully stocked kitchen and dinette, master bedroom, an eclectic second bedroom, barn doors, Smart TV and plenty of closet space, gas fireplace, swimming pool and giant waterfront backyard with lake access to swim.

4.91 out of 5 average rating, 116 reviews

The exterior of a two-story brick home features large windows framed by wooden shutters. A stone pathway leads to the entrance steps, which are flanked by neatly landscaped flower beds and ornamental plants in decorative pots. The entrance is inviting, with a warm color palette.

Home in Malden

The Ambassador Estate Inn

A warm “welcome back” to all our previous guests and “greetings” to our new friends! A luxurious executive 7 bedroom estate property located on Windsor’s finest golf course and minutes from the Ambassador Bridge to Detroit Michigan. A beautifully appointed home nestled among rare Carolinian Forest. All the amenities of a 5 star resort with the privacy and serenity of a country estate. If you are looking for quality and relaxing luxury, then look no further than the Ambassador Estate.

An indoor swimming pool is set within a bright space featuring a high ceiling. Large windows line the walls, allowing natural light to fill the area. A stone fireplace is positioned at one end, providing a cozy focal point.

4.66 out of 5 average rating, 68 reviews

ultimate getaway

Get ready for the ULTIMATE getaway! this ppty features a beautiful indoor pool , big back yard a gazebo and a gas fire place, this ppty is close to all amenities lots of restaurants and shopping around and right across from the airport , the indoor pool is heated only in the winter and fall from the month of oct till may and temp is set to 84 degrees .it is for a single family enjoyment and NOT A PARTY VENUE , THERE IS A 2000 DOLLAR PENALTY IF A PARTY TAKES PLACE AT THIS PPTY.

4.92 out of 5 average rating, 398 reviews

A serene outdoor space features a salt-water pool surrounded by lush greenery, lounge chairs, and shaded seating areas. Natural stone accents are present near the water's edge, with steps leading up to a covered patio area. Tree silhouettes frame the background, enhancing the tranquil setting.

Guest suite in Windsor

Lakeshore Hidden Oasis (heated pool / jacuzzi)

Located in Lakeshore, minutes from Windsor / Detroit, a perfect oasis for the couple looking for a quiet escape. The suite's private jacuzzi tub makes it the ideal place in any season! The suite is fully equipped, including a complete kitchenette, Smart TV, etc. A private BBQ is at your door. During your stay you will have access, day and night, to our heated salt water pool. It is open from mid March to early November at 32°C (90°F). The hot tub is open year round.

A spacious living room features a large gray sectional sofa, two mustard yellow armchairs, and a round coffee table. Natural light brightens the space through large windows, enhancing the light-colored walls and wooden flooring. A lush green plant adds a touch of nature to the decor.

4.96 out of 5 average rating, 27 reviews

Main Unit Luxury South Windsor Oasis

Welcome to your Southwood Lakes retreat ✨ A true luxury oasis with a private heated pool, where you can relax and unwind with loved ones. Centrally located, our home offers easy access to Windsor Airport, the Ambassador Bridge (12 minutes), and nearby conveniences like Costco, Starbucks, Devonshire Mall, and Caesars Casino. Enjoy full privacy: private entrance, backyard, and pool. Basement is owner-occupied, no shared spaces • Smoke-Free Home — Outdoor Smoking Only

A modern retreat is highlighted by a sleek, heated pool reflecting the evening sky. Floor-to-ceiling windows provide glimpses of illuminated indoor spaces, while a rooftop terrace is accessible. A landscaped patio is bordered by a wooden fence, offering privacy.

4.58 out of 5 average rating, 19 reviews

Architectural Gem | Direct-Entry Pool

Welcome to Windsor’s hidden gem. This modern 2-bedroom retreat stuns with a unique sunken living room, soaring patio doors, and a heated pool just steps away. The main floor features an open-concept layout with a sleek kitchen and access to a tree-top terrace lounge. Upstairs, unwind in a spa-like bedroom with a soaker tub, rainfall shower, and rooftop retreat. With two private terraces and unforgettable design, this is more than a stay—it’s an experience.

An aerial view presents a well-maintained raised ranch surrounded by a residential neighborhood. Lush green lawns and various trees create a tranquil setting, while several homes with varied architectural styles can be seen in the background. A driveway leads to the main entrance of the house.

4.86 out of 5 average rating, 22 reviews

LaSalle Retreat|Full Home2Suites

Forget your worries in this spacious and serene space. This beautiful raised ranch features 4 spacious bedrooms, 2 full bathrooms, 2 fully equipped kitchens, and 2 laundry areas—perfect for groups or multi-family stays. The bright, open layout and separate entrances offer privacy and flexibility. Enjoy the quiet, beautiful neighborhood—an ideal place to relax and unwind. Whether you’re here to relax or for a work trip, come and enjoy your stay.

5 out of 5 average rating, 5 reviews

A spacious living area features a comfortable sofa and loveseat, complemented by decorative pillows. A wooden coffee table sits in front, with a remote control placed on top. Nearby, a dining table with four chairs is visible, alongside bar stools positioned at a countertop.

Apartment in Tecumseh

Impressive Furnished All-inclusive Apartment

Welcome to your peaceful retreat! This 2-bedroom, 2-bathroom apartment is located in a calm and quiet building close to the waterfront, shops, and restaurants. Enjoy seasonal access to an outdoor pool and tennis courts, perfect for unwinding. The apartment is stocked with essentials, making it a comfortable choice for business travelers, family visits, or anyone seeking a relaxing break. Settle in and make yourself at home

4.96 out of 5 average rating, 28 reviews

A spacious living room features a large sectional couch and a coffee table, with a television displaying a beach scene. Bright natural light enters through the window, which is complemented by light curtains. The polished wooden floor adds warmth to the space.

Home in Riverside

Spacious Family Getaway w/ Pool -Sleeps 12 - 2 TVs

Welcome to our family home nestled in the quiet neighbourhood of Riverside, Windsor. Enjoy the private, fenced-in backyard with an above ground pool, a fully equipped kitchen, 7 beds that sleep 12 in total, in-suite laundry, parking for 3 mid-size cars and garage access and plenty of space for entertaining. Our home is about 13km from the Windsor International Airport, and close to many grocery stores and restaurants.

Popular amenities for Windsor rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.85 out of 5 average rating, 61 reviews

A modern living room features two black leather sofas positioned adjacent to a glass-top coffee table. The space is illuminated by natural light through two windows, accented by light grey walls and a plush area rug underneath.

Home in Detroit

Cute & Cozy 3bdrm, 1 bath. 12 mins to Downtown.

The exterior of a two-story brick house is showcased, featuring symmetrical windows and a prominent entrance flanked by greenery. The well-maintained lawn is complemented by decorative shrubs and stones, while a parked car is visible in the driveway leading to a two-car garage.

4.63 out of 5 average rating, 27 reviews

Memories to Remember/free parking/upper unit

4.94 out of 5 average rating, 17 reviews

A heated sports pool, surrounded by a spacious patio area, is complemented by comfortable seating options including loungers and umbrellas. A contemporary pool house with large windows is visible in the background, featuring a clean design that enhances the outdoor space.

Home in Belle River

The Grand River Retreat. Pool/ hot tub avail Sep

4.86 out of 5 average rating, 96 reviews

A two-story cottage with a light grey exterior is showcased, featuring a welcoming front porch with white railings. A spacious yard surrounds the home, with a gravel driveway leading up to it. Lush green grass complements the serene environment.

Home in Amherstburg

Cottage Escape by the Water

The exterior of a single-story home is shown, featuring a spacious driveway lined with paving stones. Lush greenery, including a large evergreen tree and manicured shrubs, frames the entrance, which includes a blue door and large front windows under a lightly clouded sky.

4.58 out of 5 average rating, 31 reviews

Luxury at its finest (Windsor) Swimming Pool

4.9 out of 5 average rating, 29 reviews

A modern kitchen area is highlighted with a central island, pendant lighting, and a small dining space. The room features large windows providing natural light, with a view of the outdoors. Stylish blue chairs add a pop of color against light wood flooring.

Home in Kingsville

Modern lake-town cottage

4.84 out of 5 average rating, 51 reviews

A spacious home is illuminated by exterior lighting, featuring a covered patio and large windows that showcase the interior. Lush green grass surrounds a swimming pool in the backyard, reflecting the evening sky, contributing to a serene setting.

Home in Amherstburg

Little heaven

4.85 out of 5 average rating, 74 reviews

A vibrant outdoor area features a pool surrounded by sun loungers and colorful chairs. String lights adorn the space, enhancing the evening ambiance. A pool table is positioned nearby, offering additional recreational options. The backdrop includes a spacious house with multiple windows reflecting soft twilight.

Home in Remington Park

Staycation Windsor

Other holiday rentals with a pool

An indoor heated pool is framed by light-colored walls and features a gentle slide. Basketball equipment is positioned near the edge, alongside potted plants that add a touch of greenery. Natural light fills the space through large windows.

Home in Harrow

4.75 out of 5 average rating, 83 reviews

Cheerful 5 bedroom home | Heated Indoor Pool!

4.8 out of 5 average rating, 15 reviews

A comfortable living space is presented with a gray sofa and armchair facing a modern electric fireplace. Two windows are adorned with decorative curtains, allowing natural light to fill the room. A square coffee table with a decorative piece sits in the center.

Cottage in Belle River

Rochester Place Resort 603

A living area is presented with a rich green wall, featuring a wall-mounted television and a stylish wooden cabinet. Plush blue and brown seating options encircle a circular coffee table, with a decorative centerpiece adding character. A patterned area rug complements the space.

Apartment in Lafayette Park

5 out of 5 average rating, 3 reviews

Downtown Private Escape w/city views

The modern cottage features a combination of dark blue and wood paneling, surrounded by greenery and decorative shrubs. A vibrant red umbrella offers shade near the entrance, while flat stones create a pathway leading to the front door, enhancing the welcoming exterior.

4.95 out of 5 average rating, 37 reviews

Beautiful modern cottage located on a golf course

A modern cottage is nestled among trees, featuring a light exterior with large windows. Outdoor seating areas are set with metallic chairs and tables, while a patio umbrella stands nearby. The surrounding greenery enhances the serene outdoor setting.

4.81 out of 5 average rating, 91 reviews

Rochester Place Golf Club& Resort #715 (#16) WIFI

A serene view of the illuminated pool surrounded by a partially landscaped patio area. Lounge chairs are arranged beside the pool, with soft lighting reflecting off the water. Trees and a fence frame the background, adding privacy to the outdoor space.

4.73 out of 5 average rating, 15 reviews

Luxury Modern smart home for vacation

A two-story house is set against a backdrop of tall trees, with a well-maintained lawn leading up to the entrance. The home's covered porch features white columns, and large windows reflect the daylight. A paved path runs alongside the house.

5 out of 5 average rating, 5 reviews

River front view